Taking Notes in Remote One on Ones

Before most of the software engineering world quickly pivoted to remote work in 2020, I was an advocate for the one-on-one notebook. In fact, I had a notebook that I carried with me everywhere. Medium-sized with a 100 or so pages, I usually filled one up in about three months time.

For me, the appeal of one-on-one notebooks was twofold: firstly, the tactile nature of writing notes helped ensure I would remember what was discussed, and secondly, I appreciated the signal I could give to my team member that what we were talking about was worth writing down. At times, I considered carrying a laptop with me to take notes, but the physical barrier the laptop created between the two of us felt too symbolic.

The pain I felt was in parsing my notes later. I would optimistically end my day by typing up the important parts into my note-taking app. Even as I told myself the second pass at my notes would help with my memory, I struggled to justify the activity.

Working from home forced my hand. I started by trying to keep up with my notebook writing, but I quickly changed plans. To start, I was often working from a “desk” not much bigger than my laptop, so there was a slight cost increase. Then, the pain in having a laptop between my team member and I was gone. It was simply too easy to take notes on the very thing I was using for a video call. Lastly, I felt less of a connection writing in a notebook that my team member may or may not be able to actually see and recognize.

Given all of this, I moved to digital note-taking. Looking at my choices for one-on-one note taking tools, so tried a few systems out over the last fourteen months. Along the way, I landed on a few principles in choosing a tool.


  1. Transparent. I want one-on-ones to build trust. A great way to do this is to be open with how I am capturing the conversation.
  2. Collaborative. Building something together and including others’ voices is another good way to build trust.
  3. Encourage recall. I’ll reference one-one-one notes often: before the next one-one-one, if a topic comes up again, as a reminder of context during a review cycle.
  4. When is almost as important as what. The notes should tell a story. There’s context in knowing when topics were worth talking about and signal in seeing those topics change over time.

And when I consider those principles, I come up with a set of features I’m looking for in one-on-one note taking system.


  1. The system should allow me to capture the important parts and action items from a one-on-one.
  2. The system should signal to the other person in a one-on-one conversation that I am capturing the important parts to act as a signal that this conversation is important to me.
  3. The system should allow the other person to see what I’m capturing.
  4. The system should allow the other person to contribute to what is being captured.
  5. The system should allow both people to contribute asynchronously to a shared agenda.
  6. The tool should allow both people to search by content.
  7. The tool should allow both people to filter by date.


There’s quite a lot of features I considered helpful, and ultimately, I was prepared to lose a couple of them. After a while, though, I shifted my thinking from searching for a tool to creating a system, and all of a sudden, it seemed plausible I could get everything here. For instance, 3) looks like it’s asking for a tool to live update as a user is typing notes, but screen sharing could account for this use case.

Returning to the Office

I’ve done some thinking of how I’ll update my remote setup to work in the office. I’ll likely go back to my notebook. But I’ll keep the shared set of notes. I’ll probably need to come up with some way to remind folks they can access the set of notes, and that I would appreciate their editing and contributions.

What are your principles for remote one-on-one tooling? What’s your dream set up?

Dan Ubilla is obsessed with the craft of engineering management

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